Shikimic acid CAS#138-59-0
Critical Pharma Intermediate – Essential for synthesizing antiviral drugs (e.g., Tamiflu®) and antibiotics.
High-Purity Sources – Extracted from star anise (5-8% yield) or fermented (70 g/L) for scalable production.
Biotech Versatility – Engineered into crops for stress resistance and used in chiral synthesis.
Multifunctional Additive – Acts as food preservative, cosmetic brightener, and anti-inflammatory agent.
Sustainable Production – Fermentation methods reduce reliance on plant extraction, cutting costs by 80%.
Shikimic acid is a white crystalline substance with high water solubility. It derives its name from shikimi grass (Illicium anisatum), a Japanese plant from which it was initially obtained. This compound serves as a key metabolic intermediate in both plants and microorganisms.
Traditionally, the primary source of shikimic acid has been the dried ripe fruits of Illicium species, particularly Japanese star anise (Illicium anisatum). However, recent studies have explored alternative extraction methods, including isolating shikimic acid from the fruits of sweetgum trees (Liquidambar formosana) and pine needles.
A white crystalline cyclohexene carboxylic acid with high water solubility (180 g/L at 20°C), named after Japanese shikimi grass (Illicium anisatum). This key metabolic intermediate features three chiral centers (3R,4S,5R configuration) and serves as the biochemical precursor to aromatic amino acids (phenylalanine, tyrosine, tryptophan) in the shikimate pathway.
Key Properties & Specifications
Parameter | Value |
Molecular Weight | 174.15 g/mol |
Melting Point | 185-187°C (decomp.) |
Specific Rotation | [α]₂₀ᴰ = -171° (c=1, H₂O) |
pKa Values | pKa₁=4.04, pKa₂=5.85 |
Log P (octanol-water) | -1.38 |
UV Absorption | λ<sub>max</sub> = 214 nm |
Thermal Stability | Degrades >200°C |
Production Methods & Sources
1. Traditional Plant Extraction
Source | Shikimic Acid Yield | Extraction Process |
Japanese Star Anise (Illicium anisatum) | 3-5% dry weight | - Acid hydrolysis (H₂SO₄) |
Chinese Star Anise (I. verum) | 5-8% dry weight | - Ethanol reflux |
Sweetgum (Liquidambar spp.) | 1.2-2.1% dry weight | - Alkaline hydrolysis |
Pine Needles (Pinus spp.) | 0.3-0.8% dry weight | - Supercritical CO₂ extraction |
2. Fermentation (Dominant Industrial Method)
Engineered E. coli: Yields >70 g/L (glucose feedstock)
Strain: E. coli K12/ΔaroL/ΔaroK
Fermentation: 37°C, pH 7.0, 60 hrs
3. Chemical Synthesis
Asymmetric Route: Diels-Alder of furan with acrylic acid (enantiomeric excess >98%)
Cost: $2,500/kg (vs. $400/kg for fermentation)
Industrial Applications
1. Pharmaceutical Synthesis
Oseltamivir Phosphate (Tamiflu®):
Key intermediate: 70% of global SA demand
Reaction:
Shikimate→10 stepsOseltamivirShikimate10stepsOseltamivir
Antivirals: Zanamivir (Relenza®), Peramivir
Antibiotics: Chloramphenicol, Mycobacterium inhibitors
2. Biotechnology
Shikimate Pathway Engineering: CRISPR-modified crops (drought-resistant maize)
Biocatalysis: Chiral synthon for unnatural amino acids
3. Food & Agriculture
Plant Elicitor: Enhances phenolic compound production in grapes (wine quality)
Preservative: Inhibits E. coli O157:H7 (MIC = 12.5 mg/mL)
4. Cosmetics
Skin Brightener: Tyrosinase inhibitor (0.5-2% in serums)
Anti-Inflammatory: Reduces TNF-α in keratinocytes
Technical Grades & Specifications
Grade | Purity | Key Impurities | Applications |
Pharma Grade | >99.5% | Aromatic AA <0.1% | Antiviral synthesis |
Food Grade | >98.0% | Heavy metals <10 ppm | Functional ingredients |
Research Grade | >99.9% | Endotoxin <0.01 EU/mg | Enzyme kinetics studies |
Industrial | >95.0% | Water <0.5% | Agrochemical synthesis |
Packaging Options
Format | Capacity | Material |
Glass Vials | 1-100 g | Amber glass + PTFE seal |
HDPE Bottles | 0.5-5 kg | Nitrogen headspace |
Fiber Drums | 25 kg | Double PE liner |
Custom Bulk | >100 kg | Vacuum-sealed bags |
